EP0363046A1 - Méthode pour lubrifier un moteur à alcool, à combustion interne et à allumage par étincelle - Google Patents

Méthode pour lubrifier un moteur à alcool, à combustion interne et à allumage par étincelle Download PDF

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Publication number
EP0363046A1
EP0363046A1 EP89309605A EP89309605A EP0363046A1 EP 0363046 A1 EP0363046 A1 EP 0363046A1 EP 89309605 A EP89309605 A EP 89309605A EP 89309605 A EP89309605 A EP 89309605A EP 0363046 A1 EP0363046 A1 EP 0363046A1
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EP
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Prior art keywords
lubricating oil
derived
reaction
succinic compound
group
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EP89309605A
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German (de)
English (en)
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Richard D. Schieman
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BP America Inc
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BP America Inc
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
    • C10M129/95—Esters
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
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    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/26—Amines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
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    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/046—Overbased sulfonic acid salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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Definitions

  • branched polyamines can be represented by the formula: wherein R is an alkylene group such as ethylene, propylene, butylene and other homologues (both straight chained and branched), etc., but preferably ethylene; and x, y and z are integers, x being for example, from 4 to 24 or more but preferably from 6 to 18, y being, for example, from 1 to 6 or more but preferably from 1 to 3, and z being, for example, from 0 to 6 but preferably 0 or 1.
  • the x and y units can be sequential, alternative, orderly or randomly distributed.
  • branched polyamines can also be prepared by the following reactions:
  • one or more of the foregoing branched polyamine reactants is acyclated with a substituted succinic compound selected from the group consisting of substituted succinic acids having the structural formula and substituted succinic anhydrides having the structural formula in which structural formulas R′ is a large, substantially aliphatic hydrocarbon radical having at least about 50 carbon atoms.
  • This reaction can result in a simple acyclic diamide, a cyclic diamide, a polymeric amide or a combination of any of these types of products.
  • the amide groups have the capability for reacting further to form imide groups, a substantial number of which may indeed result from the foregoing acylation reaction. There may also be present in the acylated product an appreciable proportion of amine carboxylate salt.
  • polystyrene resin The most commonly used sources of these substantially aliphatic hydrocarbon substituents are the polyolefins. These are illustrated by polyethylene, polypropylene, polyisobutylene, etc. A particularly preferred polyolefin for this use is polyisobutylene.
  • polyisobutylene the condensation of a polyisobutylene having a molecular weight of about 750 with maleic anhydride yields an alkenyl succinic anhydride which upon further reaction with a branched polyamine produces an especially effective lubricating oil dispersant.
  • the reaction of branched polyamine and succinic compound involves a splitting out of water and the reaction conditions are such that this water is removed as it is formed.
  • the first two of these reactions appear to take place spontaneously (when a substituted succinic anhydride is used) upon mixing but the third requires heating. Temperatures within the range of about 80 o C. to about 200 o C. are generally satisfactory and within this range it is preferred to use a reaction temperature of from about 100 o C. to about 160 o C. A useful method of carrying out this step is to add some toluene to the reaction mixture and to remove the water by azeotropic distillation.
  • acylated branched polyamine dispersant can be added to conventional base oils in widely varying amounts, for example, from about 0.001 to about 25% by weight of base oil.
  • the dispersant is used in amounts ranging from about 0.01 to 15%, and more preferably in amounts ranging from about 0.1 to 10%, by weight of the total composition.
  • additives include, for example, detergents of the ash-containing type, dispersants of the ashless-type, viscosity index improving agents, pour-­point depressing agents, anti-foam agents, rust-inhibiting agents oxidation and corrosion inhibiting agents, and various mixtures of these materials in various proportions.
  • the ash-containing detergents can be illustrated by the oil soluble neutral and basic salts of the alkali or alkaline earth metals of the sulfonic acids, carboxylic acids, or the organic phosphorus acids. Calcium and magnesium sulfonates are preferred.
  • basic salt is intended to include the metal salts where the metal is present in stoichiometrically larger amounts than the organic acid radical.
  • the commonly employed methods for preparing the basic salts comprises heating a mineral oil solution of the acid with a stoichiometric excess of a metal neutralizing agent, e.g., a metal oxide, hydroxide, carbonate, bicarbonate, sulfide, etc., at temperatures above about 50 o C.
  • a metal neutralizing agent e.g., a metal oxide, hydroxide, carbonate, bicarbonate, sulfide, etc.
  • various promoters can be used in the neutralizing process to aid in the incorporation of the large excess of metal.
  • These promoters are presently known and include such compounds as the phenolic substances, e.g., phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol and the various condensation products of formaldehyde with a phenolic substance, e.g., alcohols such as methanol, 2-propanol, octyl alcohol, Cellosolve, Carbitol, ethylene glycol, stearyl alcohol and cyclohexyl alcohol; and, amines such as aniline, phenylenediamine, phenothiazine, phenyl-beta-naphthylamine and dodecyl amine, etc.
  • phenolic substances e.g., phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol and the various condensation products of formaldehyde with a phenolic substance
  • alcohols such as methanol, 2-propanol, oct
  • Detergent additives derived from the partial or complete esterification of a polyhydric alcohol with any of the succinic compounds described herein can also be incorporated into the base lubricating oil.
  • Suitable polyhydric alcohols include glycols such as ethylene glycol, diethylene glycol, triethylene glycol, butylene glycol, glycerol, sorbitol, pentaerythritol, and the like.
  • the lubricating compositions employed in the method of this invention can also contain metal detergent additives in amounts usually within the range of from about 0.001% to about 15% by weight.
  • the lubricant base oils utilized herein include those of the solvent-refined or acid-refined mineral lubricating oils of the paraffinic, naphthenic or mixed paraffinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale or also useful base oils.
  • the alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. comprise another class of synthetic lubricating oils which are useful herein. These are exemplified by the oils prepared by polymerization of ethylene oxide, propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methylpolyisopropylene glycol ether having an average molecular weight of 1000, diphenyl ether of polyethylene glycol having a molecular weight of 500 to 1000, diethyl ether of polypropylene glycol having a molecular weight of 1000 to 1500, etc.) or mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C3-C3 fatty acid esters, or the C13Oxo acid diester of tetraethylene glycol.
  • esters include dibutyl adipate, di(2-ethylhexyl)-sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisoctyl azelate, dii odocyl azelate, dioctyl phthalate, didecyl phthalate, dieicoxyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, the complex ester formed by reacting one mole of sebacic acid with two moles of 2-ethyl-hexanoic acid, and the like.
  • Silicone-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils comprise another useful class of synthetic lubricants (e.g., tetraethyl-silicate, tetraisopropyl­silicate, tetra-(2-ethylhexyl)-silicate, tetra-(4-methyl-­ 2-tetraethyl)silicate, tetra(p-tert-butylphenyl)-silicate, hexyl-(4-methyl-2-pentoxy)-disiloxane, poly(methyl)-­siloxanes, poly(methylphenyl)-siloxanes, etc.).
  • synthetic lubricants e.g., tetraethyl-silicate, tetraisopropyl­silicate, tetra-(2-ethy
  • liquid esters of phosphorus-containing acids e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decane phosphonic acid, etc.
  • polymeric tetrahydrofurans e.g., polymeric tetrahydrofurans, and the like.
  • This example illustrates the lubricating method of the present invention which utilizes a known lubricating oil composition containing a branched polyamine component (Lubricating Oil A) and compares the performance of such lubricating oil composition with three other known lubricating oil compositions which lack such branched polyamine component (Lubricating Oils B, C and D).
  • the lubricating oils were tested for 16 hrs. operation in a conventional 2.3 liter 4 cylinder engine whose carburetor was modified in a known manner to permit operation of the engine on the partially vaporized methanol/air mixture used for the tests.
  • Lubricating Oil compositions were formulated with the same 300 SEN base oil and contained similar additive packages except that Lubricating Oil A contained a dispersant derived from the reaction of polyisobutylene succinimide and a branched polyamine and Lubricating Oils B, C and D contained a dispersant derived from the reaction of polyisobutylene succinic acid and a linear amine.
  • Lubricating Oil A contained a dispersant derived from the reaction of polyisobutylene succinimide and a branched polyamine
  • Lubricating Oils B, C and D contained a dispersant derived from the reaction of polyisobutylene succinic acid and a linear amine.
  • Lubricating Oil A resulted in far less engine wear after 16 hrs. of continuous engine operation than any of Lubricating Oils B, C and D.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Lubrication Of Internal Combustion Engines (AREA)
EP89309605A 1988-09-21 1989-09-21 Méthode pour lubrifier un moteur à alcool, à combustion interne et à allumage par étincelle Ceased EP0363046A1 (fr)

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US24741988A 1988-09-21 1988-09-21
US247419 1988-09-21

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EP0363046A1 true EP0363046A1 (fr) 1990-04-11

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0462319A1 (fr) * 1990-06-20 1991-12-27 The Lubrizol Corporation (an Ohio corporation) Lubrifiants, dispositifs pour lubrifiants, et méthode pour lubrifier à l'aide d'un carter des moteurs à combustion interne utilisant un alcool comme carburant par injection

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090156445A1 (en) * 2007-12-13 2009-06-18 Lam William Y Lubricant composition suitable for engines fueled by alternate fuels

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4234435A (en) * 1979-02-23 1980-11-18 The Lubrizol Corporation Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation
EP0067002A1 (fr) * 1981-05-26 1982-12-15 The Lubrizol Corporation Compositions contenant du bore utiles comme additifs pour lubrifiants
WO1986005501A1 (fr) * 1985-03-14 1986-09-25 The Lubrizol Corporation Condensats et carburants contenant de l'azote de poids moleculaire eleve et lubrifiants les contenant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4234435A (en) * 1979-02-23 1980-11-18 The Lubrizol Corporation Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation
EP0067002A1 (fr) * 1981-05-26 1982-12-15 The Lubrizol Corporation Compositions contenant du bore utiles comme additifs pour lubrifiants
WO1986005501A1 (fr) * 1985-03-14 1986-09-25 The Lubrizol Corporation Condensats et carburants contenant de l'azote de poids moleculaire eleve et lubrifiants les contenant

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0462319A1 (fr) * 1990-06-20 1991-12-27 The Lubrizol Corporation (an Ohio corporation) Lubrifiants, dispositifs pour lubrifiants, et méthode pour lubrifier à l'aide d'un carter des moteurs à combustion interne utilisant un alcool comme carburant par injection
AU625351B2 (en) * 1990-06-20 1992-07-09 Lubrizol Corporation, The Lubricating oil compositions for MeOH-fueled diesel engines
US5422022A (en) * 1990-06-20 1995-06-06 The Lubrizol Corporation Lubricants, lubricant additives, and methods for lubricating sump-lubricated fuel-injected alcohol-powered internal combustion engines

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